Sure, Hilton Head might be famous for the golf courses and tournaments held here. This little slice of heaven may be recognized as a Gold Level Bicycle Friendly Community. But everyone knows what really brings people to the island are the beaches and the sparkling waters that stretch out beyond them. What better way to see those beautiful waters than on an exhilarating Hilton Head sailing excursion? There’s one for everyone, no matter how stable your sea legs may be!
SUMO Trimaran Sailing Experience
If speed gets your heart racing, meet SUMO. This 38-foot trimaran holds the title of fastest sailboat on the island. With three sleek hulls and big trampoline decks, it’s designed for adrenaline and relaxation in equal measure. Step inside and you’ll find a comfy cabin with seating, a kitchen space, and even a bathroom. Up top, stretch out in the sun, or scan the water for dolphins, sea turtles, and the lucky sighting of a manatee. Sailing out of Harbour Town Yacht Basin, SUMO carries up to six guests. A 1.5-hour private day sail is $325, while a two-hour sunset cruise is $425. Pack your drinks, bring a few snacks, and let SUMO deliver the views.
Stars & Stripes America’s Cup Tour
The Stars & Stripes isn’t just any sailboat. It’s a legendary 12-meter racing yacht once steered by Dennis Conner, “Mr. America’s Cup” himself. Today, this 65-foot beauty glides through Calibogue Sound, giving guests a rare chance to step aboard a true icon of sailing history. Setting sail out of Harbour Town, the yacht still carries her original racing winches, grinders, and a mast that commands attention from shore. Grab a line and join the crew in hoisting sails, or sit back with the breeze in your hair while the team does the heavy lifting. Public sails run $50 per person by day and $70 at sunset, while private charters welcome up to 28 passengers for $1,400.
Private Dolphin Watching & Wildlife Sail
Looking for a calmer sail? Step aboard Spartina. This 27-foot Stiletto catamaran is designed for comfort with cushioned benches and beanbag seating. Thanks to its shallow draft, you’re just a few feet above the water, making dolphin encounters feel up close and personal. Every trip is private for up to six guests, offering a laid-back journey through Broad Creek’s winding marshes. Expect plenty of wildlife and a captain who knows the waters inside out. Departing from Shelter Cove Harbour & Marina, Spartina offers a two-hour dolphin day sail for $359, a sunset sail for $399, and a special Tuesday night fireworks cruise for $479.
Hilton Head Sunset Cruises
Meet Rosé, the shining new 36-foot sailing catamaran in the Island Head Sailing fleet. Big deck. Soft seating. Easygoing vibe. This boat is made for social cruising, whether it’s sipping mimosas in the morning, catching golden-hour glow with a glass of rosé, or just soaking in the scenery with friends. Rosé carries up to 24 passengers and sails out of Broad Creek Marina. Signature trips include Brunch Under Sail ($89), a daytime sail ($69), golden-hour with rosé and appetizers ($99), and the always-popular Tuesday night fireworks sail ($89).
Whatever your water-loving heart desires, there is a sailing experience here that awaits. Just because summer is winding down, doesn’t mean the fun has to! There’s still plenty of time to squeeze in a long weekend!